Senior Spotlight

The Winter Auxiliary # 303 and Loretta Auxiliary # 394 have very graciously sponsored two of our students, Kady Granica and Reiley Kavanaugh, to attend Badger Girls State this summer in Oshkosh. This program is a practical civics conference that allows students to learn about stat government by actively participating in it. Congratulations girls for being chosen to attend, and a big thank you to the Winter Auxiliary for sponsoring both of them!

Coach Delabar, Coach Carrie, and 12 Winter School District student athletes attended the second annual Leadership Summit held at Lake Holcombe High School on Thursday.
The summit speaker, Duane Jourdeans of Upward Spiral Consulting, focused his teaching on Emotional Intelligence and training your mind as an athlete, student, employee, and beyond. His message was very thought provoking and sparked some great conversation amongst the 200 or so student athletes in attendance!





8th Grade Promotion for the Class of 2029!

Middle School Academic & PBIS Celebration

Yearbooks for Sale! Please contact the District Office or Alicia Lueloff if interested.

May Student of the Month

Senior Spotlight

Senior Spotlight

Senior Spotlight

Important Information

Senior Spotlight

Senior Spotlight

Senior Spotlight

Senior Spotlight

Student of the Month
May 2025
Summer Block
Class of 2025
Summer Block, daughter of Brady Block, has
been selected as the Winter High School
Student of the Month for May 2025!
Summer is a high school senior, graduating
this month. She is a diligent student who
always completes high quality work. While in
High School she has been a three-season
athlete, participating in volleyball, basketball,
track and softball. Summer is an outstanding
volleyball player, as evident by her earning
the East Lakeland Conference Volleyball
Player of the Year. Summer is also a member
of the East Lakeland National Honor Society
and helped at Project Northwoods Nature
Center through the science internship.
After high school Summer plans on attending
the University of Wisconsin- Lacrosse to
pursue a degree in Psychology.
Mr. Suralski, Winter High School’s Social
Studies teacher, says, “Summer has always
been a very conscientious, polite, and high
achieving student. She is very dedicated and
self motivated, definitely not someone I have ever had to remind about missing assignments or
deadlines.”
Congratulations to Summer for earning Student of the Month for May 2025!

Craig and his wife Deb moved to the Hayward area in June of 2001. Craig spent the first six
years of his administrative career as the Hayward Middle School Assistant Principal. Craig then
moved into to the Principal role at the middle school where he spent four years. He was then
asked to move into the Superintendent role where he has spent the last 14 years.
Before moving to Hayward, Craig was a teacher and football, wrestling, and baseball coach at
Freedom, Merrill, and Mosinee. Throughout his career, Craig has had the privilege to serve on
numerous elected boards. Currently Craig is serving on the Wisconsin Association of School
District Administrators Board of Control and also the WIAA Advisory Committee. Craig also is
currently serving on the WIAA Conference Realignment Committee.
Craig is both excited and humbled to be part of the Winter School District and is looking
forward to serving this great community. His official start date is July 1 st and he can’t wait to
meet everyone in the community and get to WORK! on assuring every student has the best
opportunity to accomplish their individual goals.

Reminder about the upcoming Middle School/High School Band Concert. This includes 5th grade.

Youth apprenticeships allow students to gain real-world experience in their chosen field. This practical approach provides them with the skills and knowledge needed to perform tasks effectively in a professional environment. We are proud to be having this experience for our students! Thank you Ashley and Madison for bringing your work into our school!

Please give a warm welcome to our new Superintendent, Craig Olson. Welcome to the Winter School District!


